US4188475A - Process for the preparation of flame-retardant polycarbonates - Google Patents
Process for the preparation of flame-retardant polycarbonates Download PDFInfo
- Publication number
- US4188475A US4188475A US05/920,932 US92093278A US4188475A US 4188475 A US4188475 A US 4188475A US 92093278 A US92093278 A US 92093278A US 4188475 A US4188475 A US 4188475A
- Authority
- US
- United States
- Prior art keywords
- aromatic
- mol
- chloride
- halogen
- diphenols
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 229920000515 polycarbonate Polymers 0.000 title claims abstract description 39
- 239000004417 polycarbonate Substances 0.000 title claims abstract description 39
- 238000000034 method Methods 0.000 title claims abstract description 16
- 238000002360 preparation method Methods 0.000 title claims abstract description 6
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 title description 4
- 239000003063 flame retardant Substances 0.000 title description 4
- 125000003118 aryl group Chemical group 0.000 claims abstract description 24
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 238000006116 polymerization reaction Methods 0.000 claims description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- XKZQKPRCPNGNFR-UHFFFAOYSA-N 2-(3-hydroxyphenyl)phenol Chemical compound OC1=CC=CC(C=2C(=CC=CC=2)O)=C1 XKZQKPRCPNGNFR-UHFFFAOYSA-N 0.000 claims 1
- 101150108015 STR6 gene Proteins 0.000 claims 1
- 239000002253 acid Substances 0.000 abstract description 4
- 150000001805 chlorine compounds Chemical class 0.000 abstract description 4
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- -1 preferably C1 to C4 Chemical group 0.000 description 6
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical class ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 5
- NYIBPWGZGSXURD-UHFFFAOYSA-N 3,4-dichlorobenzenesulfonyl chloride Chemical compound ClC1=CC=C(S(Cl)(=O)=O)C=C1Cl NYIBPWGZGSXURD-UHFFFAOYSA-N 0.000 description 4
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 4
- KYPYTERUKNKOLP-UHFFFAOYSA-N Tetrachlorobisphenol A Chemical compound C=1C(Cl)=C(O)C(Cl)=CC=1C(C)(C)C1=CC(Cl)=C(O)C(Cl)=C1 KYPYTERUKNKOLP-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 description 2
- ODJUOZPKKHIEOZ-UHFFFAOYSA-N 4-[2-(4-hydroxy-3,5-dimethylphenyl)propan-2-yl]-2,6-dimethylphenol Chemical compound CC1=C(O)C(C)=CC(C(C)(C)C=2C=C(C)C(O)=C(C)C=2)=C1 ODJUOZPKKHIEOZ-UHFFFAOYSA-N 0.000 description 2
- ZLYBFBAHAQEEQQ-UHFFFAOYSA-N 4-chlorobenzenesulfonyl chloride Chemical compound ClC1=CC=C(S(Cl)(=O)=O)C=C1 ZLYBFBAHAQEEQQ-UHFFFAOYSA-N 0.000 description 2
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- SDDLEVPIDBLVHC-UHFFFAOYSA-N Bisphenol Z Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)CCCCC1 SDDLEVPIDBLVHC-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- ACWQBUSCFPJUPN-HYXAFXHYSA-N Tiglic aldehyde Chemical compound C\C=C(\C)C=O ACWQBUSCFPJUPN-HYXAFXHYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 244000309464 bull Species 0.000 description 2
- OPECTNGATDYLSS-UHFFFAOYSA-N naphthalene-2-sulfonyl chloride Chemical compound C1=CC=CC2=CC(S(=O)(=O)Cl)=CC=C21 OPECTNGATDYLSS-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 230000005501 phase interface Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- MPJLLBLFMGXUNW-UHFFFAOYSA-N 1,3,5-tribromocyclohexa-2,4-dien-1-ol Chemical compound OC1(Br)CC(Br)=CC(Br)=C1 MPJLLBLFMGXUNW-UHFFFAOYSA-N 0.000 description 1
- FREOGXBZEAMJQN-UHFFFAOYSA-N 2,4-dimethylbenzenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C(C)=C1 FREOGXBZEAMJQN-UHFFFAOYSA-N 0.000 description 1
- BXCOSWRSIISQSL-UHFFFAOYSA-N 2,5-dichlorobenzenesulfonyl chloride Chemical compound ClC1=CC=C(Cl)C(S(Cl)(=O)=O)=C1 BXCOSWRSIISQSL-UHFFFAOYSA-N 0.000 description 1
- BLDLRWQLBOJPEB-UHFFFAOYSA-N 2-(2-hydroxyphenyl)sulfanylphenol Chemical class OC1=CC=CC=C1SC1=CC=CC=C1O BLDLRWQLBOJPEB-UHFFFAOYSA-N 0.000 description 1
- KMVZDSQHLDGKGV-UHFFFAOYSA-N 2-chlorobenzenesulfonyl chloride Chemical compound ClC1=CC=CC=C1S(Cl)(=O)=O KMVZDSQHLDGKGV-UHFFFAOYSA-N 0.000 description 1
- LIZNEYWXYFVEBF-UHFFFAOYSA-N 2-ethylbenzenesulfonyl chloride Chemical compound CCC1=CC=CC=C1S(Cl)(=O)=O LIZNEYWXYFVEBF-UHFFFAOYSA-N 0.000 description 1
- HDECRAPHCDXMIJ-UHFFFAOYSA-N 2-methylbenzenesulfonyl chloride Chemical compound CC1=CC=CC=C1S(Cl)(=O)=O HDECRAPHCDXMIJ-UHFFFAOYSA-N 0.000 description 1
- YMTYZTXUZLQUSF-UHFFFAOYSA-N 3,3'-Dimethylbisphenol A Chemical compound C1=C(O)C(C)=CC(C(C)(C)C=2C=C(C)C(O)=CC=2)=C1 YMTYZTXUZLQUSF-UHFFFAOYSA-N 0.000 description 1
- GNYVVCRRZRVBDD-UHFFFAOYSA-N 3-chloro-4-methylbenzenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1Cl GNYVVCRRZRVBDD-UHFFFAOYSA-N 0.000 description 1
- OINWZUJVEXUHCC-UHFFFAOYSA-N 3-chlorobenzenesulfonyl chloride Chemical compound ClC1=CC=CC(S(Cl)(=O)=O)=C1 OINWZUJVEXUHCC-UHFFFAOYSA-N 0.000 description 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
- LACFLXDRFOQEFZ-UHFFFAOYSA-N 4-ethylbenzenesulfonyl chloride Chemical compound CCC1=CC=C(S(Cl)(=O)=O)C=C1 LACFLXDRFOQEFZ-UHFFFAOYSA-N 0.000 description 1
- VHBFBNCERXCECQ-UHFFFAOYSA-N 5-chloro-2-methylbenzenesulfonyl chloride Chemical compound CC1=CC=C(Cl)C=C1S(Cl)(=O)=O VHBFBNCERXCECQ-UHFFFAOYSA-N 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- GIXXQTYGFOHYPT-UHFFFAOYSA-N Bisphenol P Chemical compound C=1C=C(C(C)(C)C=2C=CC(O)=CC=2)C=CC=1C(C)(C)C1=CC=C(O)C=C1 GIXXQTYGFOHYPT-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 101100386054 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) CYS3 gene Proteins 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- BQPJFNZAKMDFBG-UHFFFAOYSA-N anthracene-1-sulfonyl chloride Chemical class C1=CC=C2C=C3C(S(=O)(=O)Cl)=CC=CC3=CC2=C1 BQPJFNZAKMDFBG-UHFFFAOYSA-N 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical group C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- DASJFYAPNPUBGG-UHFFFAOYSA-N naphthalene-1-sulfonyl chloride Chemical class C1=CC=C2C(S(=O)(=O)Cl)=CC=CC2=C1 DASJFYAPNPUBGG-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- YYSWKSJKAKNXHB-UHFFFAOYSA-N phenanthrene-1-sulfonyl chloride Chemical class C1=CC2=CC=CC=C2C2=C1C(S(=O)(=O)Cl)=CC=C2 YYSWKSJKAKNXHB-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 101150035983 str1 gene Proteins 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/04—Aromatic polycarbonates
- C08G64/06—Aromatic polycarbonates not containing aliphatic unsaturation
- C08G64/14—Aromatic polycarbonates not containing aliphatic unsaturation containing a chain-terminating or -crosslinking agent
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/04—Aromatic polycarbonates
- C08G64/06—Aromatic polycarbonates not containing aliphatic unsaturation
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S260/00—Chemistry of carbon compounds
- Y10S260/24—Flameproof
Definitions
- the present invention relates to the preparation of aromatic polycarbonates, by the known two-phase interface process, from diphenols, preferably from halogen-free diphenols, characterized in that aromatic monosulphonic acid chlorides are used as chain stoppers in amounts of about 2 mol % to 20 mol %, preferably in amounts of about 2.5 mol % to 10 mol %, relative to mols of the diphenols employed.
- the present invention relates to the aromatic polycarbonates obtainable by the process according to the invention.
- the polycarbonates according to the invention have an improved flame repellency. Improvements in the flame-retardant properties of aromatic thermoplastic polycarbonates have already been attempted in various ways, and also achieved; however, occasionally disadvantages in other polycarbonate properties had to be accepted with the flame retardant improvement.
- aromatic monosulphonic acid chlorides for the process according to the invention; thus, for example, unsubstituted and substituted benzenesulphonyl chlorides, unsubstituted and substituted naphthalenesulphonyl chlorides, unsubstituted and substituted anthracenesulphonyl chlorides and unsubstituted and substituted phenanthrenesulphonyl chlorides.
- alkyl, cycloalkyl, aryl or halogen for example, are to be understood as substituents.
- Benzenesulphonyl chlorides which are suitable according to the invention are those of the formula I ##STR1## wherein R 1 to R 5 are identical or different and are H, alkyl, preferably C 1 to C 4 , cycloalkyl, preferably C 5 to C 6 , aryl, preferably C 6 to C 16 , or halogen, preferably chlorine or bromine.
- aromatic monosulphonic acid chlorides which are suitable according to the invention are benzenesulphonyl chloride, 2-methylbenzenesulphonyl chloride, 4-methylbenzenesulphonyl chloride, 2,4-dimethylbenzenesulphonyl chloride, 4-ethylbenzenesulphonyl chloride, 2-ethylbenzenesulphonyl chloride, 2-chlorobenzenesulphonyl chloride, 3-chlorobenzenesulphonyl chloride, 4-chlorobenzenesulphonyl chloride, 2,5-dichlorobenzenesulphonyl chloride, 3,4-dichlorobenzenesulphonyl chloride, 2-methyl-5-chlorobenzenesulphonyl chloride, 3-chloro-4-methylbenzenesulphonyl chloride, diphenyl-4'-sulphonyl chloride, 3-methyl-diphenyl-4-sulphonyl chloride, 3,
- benzenesulphonyl chloride 4-methylbenzenesulphonyl chloride, 4-chlorobenzenesulphonyl chloride, 3,4-dichlorobenzenesulphonyl chloride, diphenyl-4-sulphonyl chloride and naphthalene-2-sulphonyl chloride.
- aromatic polycarbonates of the present invention can also be characterized by the general structural formula ##STR2## wherein E and E 1 are the same or different and are radicals of the formula II ##STR3## wherein R 1 to R 5 are identical or different and are H, C 1 -C 4 -alkyl, C 5 -C 6 -cycloalkyl, C 6 -C 16 -aryl or halogen, and
- Z represents a divalent aromatic radical derived from a compound of the formula III
- n is the degree of polymerization which results from a weight average molecular weight, Mw, of the aromatic polycarbonate of from about 10,000 to 100,000.
- the preparation of polycarbonates by the phase interface process is known.
- the polycarbonates are obtained by reacting diphenols, in particular dihydroxydiaryl-alkanes or -cycloalkanes, with phosgene, those dihydroxydiaryl-alkanes and -cycloalkanes in which the aryl radicals are substituted in the o-position to the phenolic hydroxyl groups also being suitable, in addition to unsubstituted dihydroxydiaryl-alkanes and -cycloalkanes.
- the polycarbonates prepared by the phase interface process can also be branched in a known manner.
- the known catalysts such as, for example, triethylamine, and the customary solvents, reaction temperatures and amounts of alkali for the two-phase interface process are likewise known such as those taught in the text Chemistry and Physics of Polycarbonates by Hermann Schnell, Interscience Publishers, New York, 1964.
- diphenols examples include hydroquinone, resorcinol, 4,4'-dihydroxydiphenyl, bis-(hydroxyphenyl) alkanes, such as, for example, C 1 -C 8 -alkylene- and C 2 -C 8 -alkylidene-bisphenols, bis-(hydroxyphenyl)-cycloalkanes, such as, for example, C 5 -C 6 -cycloalkylene- and C 5 -C 6 -cycloalkylidene-bisphenols, and bis-(hydroxyphenyl) sulphides, ethers, ketones, sulphoxides or sulphones. Furthermore, ⁇ , ⁇ '-bis-(hydroxyphenyl)-diisopropylbenzenes and the corresponding nuclear-alkylated and nuclear-halogenated compounds.
- Suitable polycarbonates are, for example, those based on 2,2-bis-(4-hydroxy-phenyl)-propane (bisphenol A), 2,2-bis-(4-hydroxy-3,5-dichloro-phenyl)-propane (tetrachlorobisphenol A), 2,2-bis-(4-hydroxy-3,5-dibromo-phenyl)-propane (tetrabromobisphenol A), 2,2-bis-(4-hydroxy-3,5-dimethyl-phenyl)-propane (tetramethylbisphenol A), 2,2-bis-(4-hydroxy-3-methyl-phenyl)-propane and 1,1-bis-(4-hydroxy-phenyl)-cyclohexane (bisphenol Z), as well as those based on trinuclear bisphenols, such as ⁇ , ⁇ '-bis-(4-hydroxy-phenyl) -p-diisopropylbenzene.
- bisphenol A 2,2-bis-(4-hydroxy-phen
- Polycarbonates obtained from halogen-free diphenols are preferred according to the invention.
- the flame-retardant polycarbonates according to the invention are distinguished by an improved flame retardancy.
- the polycarbonates according to the invention generally achieve better burning gradings and considerably shorter after-burn times.
- a solution is prepared from 3.192 kg of 2,2-bis-(4-hydroxyphenyl)-propane (bisphenol A) (14 mols), 2.53 kg of 45% strength aqueous sodium hydroxide solution and 15 liters of distilled water. After adding 34 kg of methylene chloride, 80.8 of benzenesulphonyl chloride (3.27 mol %), dissolved in 1 kg of methylene chloride, are added at room temperature, while stirring. 2.64 kg of phosgene are passed in at 20°-25° C. The pH value is kept at 13-14 during the phosgenation by adding a further 26.3 kg of 6.5% strength sodium hydroxide solution.
- the after-burn times after the 2nd flaming are determined with a stopwatch; each is the average value of 5 different measurements.
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyesters Or Polycarbonates (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19772732556 DE2732556A1 (de) | 1977-07-19 | 1977-07-19 | Verfahren zur herstellung von flammhemmenden polycarbonaten |
| DE2732556 | 1977-07-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US4188475A true US4188475A (en) | 1980-02-12 |
Family
ID=6014277
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US05/920,932 Expired - Lifetime US4188475A (en) | 1977-07-19 | 1978-06-30 | Process for the preparation of flame-retardant polycarbonates |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4188475A (enrdf_load_stackoverflow) |
| EP (1) | EP0000396B1 (enrdf_load_stackoverflow) |
| JP (1) | JPS5421497A (enrdf_load_stackoverflow) |
| DE (2) | DE2732556A1 (enrdf_load_stackoverflow) |
| IT (1) | IT1106182B (enrdf_load_stackoverflow) |
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4403087A (en) * | 1981-09-28 | 1983-09-06 | General Electric Company | Polycarbonates chain terminated with sulfonic acid salt containing phenols |
| US4469860A (en) * | 1981-09-28 | 1984-09-04 | General Electric Company | Aromatic polycarbonate resin end capped with hydroxy arylene sulfonate |
| US4471104A (en) * | 1981-12-18 | 1984-09-11 | Bayer Aktiengesellschaft | Process for the preparation of polycarbonates having sulfonanilide terminal groups |
| US4503213A (en) * | 1982-07-10 | 1985-03-05 | Bayer Aktiengesellschaft | Process for the preparation of polycarbonates having N-alkyl-perfluoroalkyl sulfonamide terminal groups |
| US4789723A (en) * | 1985-12-19 | 1988-12-06 | Enichem Tecnoresine S.P.A. | Polycarbonate branched with double-ring aromatic compound |
| US6203727B1 (en) | 1997-10-15 | 2001-03-20 | The Dow Chemical Company | Electronically-conductive polymers |
| US20070100059A1 (en) * | 2005-10-31 | 2007-05-03 | Brian Mullen | Ionizing radiation stable thermoplastic composition, method of making, and articles formed therefrom |
| US20070117957A1 (en) * | 2005-11-18 | 2007-05-24 | Brian Mullen | Ionizing radiation stable thermoplastic composition, method of making, and articles formed therefrom |
| US20080014446A1 (en) * | 2004-10-07 | 2008-01-17 | General Electric Company | Window shade and a multi-layered article, and methods of making the same |
| US20080081892A1 (en) * | 2006-09-29 | 2008-04-03 | General Electric Company | Thermoplastic compositions, methods of making, and articles formed therefrom |
| US20100075125A1 (en) * | 2008-09-25 | 2010-03-25 | Christianus Johannes Jacobus Maas | Flame retardant thermoplastic polymer composition, method of manufacture, and articles formed therefrom |
| US20100280160A1 (en) * | 2008-09-25 | 2010-11-04 | Arjan Karremans | Flame retardant thermoplastic composition and articles formed therefrom |
| US20100280159A1 (en) * | 2008-09-25 | 2010-11-04 | Christianus Johannes Jacobus Maas | Flame retardant thermoplastic composition and articles formed therefrom |
| US10472996B2 (en) | 2011-04-18 | 2019-11-12 | Holtec International | Autonomous self-powered system for removing thermal energy from pools of liquid heated by radioactive materials, and method of the same |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5625110A (en) * | 1978-12-18 | 1981-03-10 | Bristol Myers Co | Antibacterial |
| JPS60501212A (ja) * | 1983-05-04 | 1985-08-01 | ゼネラル エレクトリツク カンパニイ | 難燃性末端キヤツプポリカ−ボネ−トを含む組成物 |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1311130A (fr) | 1960-03-31 | 1962-12-07 | Teikoku Jinzo Kenshi Kk | Polyesters modifiés et procédé pour les préparer |
| US3177179A (en) * | 1960-05-31 | 1965-04-06 | Dow Chemical Co | Chain terminated polycarbonates |
| US3240756A (en) * | 1961-03-02 | 1966-03-15 | Allied Chem | Continuous addition of phenolic chain terminator in bisphenol polycarbonate production by emulsion polymerization |
| US3398120A (en) * | 1963-07-16 | 1968-08-20 | Hooker Chemical Corp | Polyesters of diacid halide, alkyl bisphenol and glycol |
| US3933734A (en) * | 1973-12-28 | 1976-01-20 | General Electric Company | Flame retardant polycarbonate composition |
| US4020045A (en) * | 1976-02-26 | 1977-04-26 | The Dow Chemical Company | Process for controlling the molecular weight of aromatic polycarbonates |
-
1977
- 1977-07-19 DE DE19772732556 patent/DE2732556A1/de not_active Withdrawn
-
1978
- 1978-06-30 US US05/920,932 patent/US4188475A/en not_active Expired - Lifetime
- 1978-07-12 EP EP78100379A patent/EP0000396B1/de not_active Expired
- 1978-07-12 DE DE7878100379T patent/DE2860055D1/de not_active Expired
- 1978-07-17 JP JP8619778A patent/JPS5421497A/ja active Granted
- 1978-07-17 IT IT50325/78A patent/IT1106182B/it active
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1311130A (fr) | 1960-03-31 | 1962-12-07 | Teikoku Jinzo Kenshi Kk | Polyesters modifiés et procédé pour les préparer |
| US3177179A (en) * | 1960-05-31 | 1965-04-06 | Dow Chemical Co | Chain terminated polycarbonates |
| US3240756A (en) * | 1961-03-02 | 1966-03-15 | Allied Chem | Continuous addition of phenolic chain terminator in bisphenol polycarbonate production by emulsion polymerization |
| US3398120A (en) * | 1963-07-16 | 1968-08-20 | Hooker Chemical Corp | Polyesters of diacid halide, alkyl bisphenol and glycol |
| US3933734A (en) * | 1973-12-28 | 1976-01-20 | General Electric Company | Flame retardant polycarbonate composition |
| US4020045A (en) * | 1976-02-26 | 1977-04-26 | The Dow Chemical Company | Process for controlling the molecular weight of aromatic polycarbonates |
Non-Patent Citations (2)
| Title |
|---|
| Chemistry and Physics of Polycarbonates, by H. Schnell Interscience Pub., 1964 (pp. 189-207). * |
| Polycarbonates, by W. M. Christopher and D. Fox, Reinhold Pub. Corp., 1962 (pp. 83-160). * |
Cited By (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4469860A (en) * | 1981-09-28 | 1984-09-04 | General Electric Company | Aromatic polycarbonate resin end capped with hydroxy arylene sulfonate |
| US4403087A (en) * | 1981-09-28 | 1983-09-06 | General Electric Company | Polycarbonates chain terminated with sulfonic acid salt containing phenols |
| US4471104A (en) * | 1981-12-18 | 1984-09-11 | Bayer Aktiengesellschaft | Process for the preparation of polycarbonates having sulfonanilide terminal groups |
| US4503213A (en) * | 1982-07-10 | 1985-03-05 | Bayer Aktiengesellschaft | Process for the preparation of polycarbonates having N-alkyl-perfluoroalkyl sulfonamide terminal groups |
| US4789723A (en) * | 1985-12-19 | 1988-12-06 | Enichem Tecnoresine S.P.A. | Polycarbonate branched with double-ring aromatic compound |
| US6203727B1 (en) | 1997-10-15 | 2001-03-20 | The Dow Chemical Company | Electronically-conductive polymers |
| US20080014446A1 (en) * | 2004-10-07 | 2008-01-17 | General Electric Company | Window shade and a multi-layered article, and methods of making the same |
| US7557153B2 (en) | 2005-10-31 | 2009-07-07 | Sabic Innovative Plastics Ip Bv | Ionizing radiation stable thermoplastic composition, method of making, and articles formed therefrom |
| WO2007053500A1 (en) * | 2005-10-31 | 2007-05-10 | General Electric Company | Ionizing radiation stable thermoplastic composition, method of making, and articles formed therefrom |
| US20070100059A1 (en) * | 2005-10-31 | 2007-05-03 | Brian Mullen | Ionizing radiation stable thermoplastic composition, method of making, and articles formed therefrom |
| US20070117957A1 (en) * | 2005-11-18 | 2007-05-24 | Brian Mullen | Ionizing radiation stable thermoplastic composition, method of making, and articles formed therefrom |
| US7528212B2 (en) | 2005-11-18 | 2009-05-05 | Sabic Innovative Plastics Ip B.V. | Ionizing radiation stable thermoplastic composition, method of making, and articles formed therefrom |
| US20080081892A1 (en) * | 2006-09-29 | 2008-04-03 | General Electric Company | Thermoplastic compositions, methods of making, and articles formed therefrom |
| US20100075125A1 (en) * | 2008-09-25 | 2010-03-25 | Christianus Johannes Jacobus Maas | Flame retardant thermoplastic polymer composition, method of manufacture, and articles formed therefrom |
| US20100280160A1 (en) * | 2008-09-25 | 2010-11-04 | Arjan Karremans | Flame retardant thermoplastic composition and articles formed therefrom |
| US20100280159A1 (en) * | 2008-09-25 | 2010-11-04 | Christianus Johannes Jacobus Maas | Flame retardant thermoplastic composition and articles formed therefrom |
| US8445568B2 (en) | 2008-09-25 | 2013-05-21 | Sabic Innovative Plastics Ip B.V. | Flame retardant thermoplastic composition and articles formed therefrom |
| US8771829B2 (en) | 2008-09-25 | 2014-07-08 | Sabic Innovative Plastics Ip B.V. | Flame retardant thermoplastic polymer composition, method of manufacture, and articles formed therefrom |
| US10472996B2 (en) | 2011-04-18 | 2019-11-12 | Holtec International | Autonomous self-powered system for removing thermal energy from pools of liquid heated by radioactive materials, and method of the same |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2732556A1 (de) | 1979-02-01 |
| JPS5421497A (en) | 1979-02-17 |
| DE2860055D1 (en) | 1980-11-13 |
| EP0000396A1 (de) | 1979-01-24 |
| IT7850325A0 (it) | 1978-07-17 |
| IT1106182B (it) | 1985-11-11 |
| EP0000396B1 (de) | 1980-07-23 |
| JPS6228809B2 (enrdf_load_stackoverflow) | 1987-06-23 |
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